Felicity Leo is a friend of mine and she writes for us here from time to time. She was in Sicily with our group in 2025, eleven days with a group of women, most of them over fifty. I asked her afterwards to write down what stayed with her, and this is it, in her own words rather than mine.
The Sabadì store on Corso San Giorgio in Modica, Sicily, near the Duomo di San Giorgio.
Photo©: Anna Fishman / Olegana Travel Boutique
Guest blog post from Felicity Leo
Authenticity. That’s the word that stayed with me long after my recent trip to Sicily. It was one of the most rewarding experiences I’ve ever had!
Early on, I realized just how special it was, so I made a conscious effort to put my phone away and truly take in the cinematic beauty around me.
Aside from a few phone camera snaps for memory’s sake, I really soaked in the cinematic beauty around me.
Piazza del Duomo on Ortigia Island in Syracuse, Sicily, framed by historic Baroque architecture.
Photo©: Anna Fishman / Olegana Travel Boutique
Traveling for eleven days with an inspiring group of women, most over 50, felt deeply real.
It wasn’t just the amazingly delicious Sicilian food, wine tasting, the expertly curated tours, or the utterly perfect boutique hotels.
It was the ease of connection, the shared laughter, and the art of traveling with intention.
The Fontana di Diana in Piazza Archimede on Ortigia Island in Syracuse, Sicily, Italy.
Photo©: Anna Fishman / Olegana Travel Boutique
From tasting heritage chocolate in Modica to sailing past Isola Bella, each day felt like a love letter to the senses.
Among cathedral spires and olive groves, I rediscovered what makes travel transformative: presence, friendship, and joy.
Your next chapter awaits
Historic SCHLOSS Roxburghe hotel and country estate near Kelso in the Scottish Borders, Scotland.
Photo©: Anna Fishman / Olegana Travel Boutique
From Anna
If Sicily was about rediscovery, there are two ways to follow it.
Sicily itself comes back in May 2028, the 16th to the 25th, and Melina and I will be hosting that one together. There is no page for it yet. If you would like to hear about it first when it opens, tell me on a call and I will make sure you do.
Before that, our Castles & Gardens tour of the United Kingdom runs May 13 to 22, 2027, for a small group of women, and I am hosting it myself.
The historic village of Castle Combe in Wiltshire, on the southern edge of the Cotswolds, England.
Photo©: Anna Fishman / Olegana Travel Boutique
It begins in the Scottish Borders, where the great houses sit in their own landscapes and the pace is set by the countryside rather than by a schedule. A drink at Floors Castle. A morning at Abbotsford House, which Walter Scott built to his own design and which is still full of his things. Then south into Northumberland for Bamburgh Castle above the North Sea, and for the Alnwick Garden, where the Poison Garden holds more than a hundred plants that could do you real harm. We tour it privately, before the gates open to everyone else. Alnwick Castle is next door, and you will recognize it as Hogwarts.
The River Avon and Bancroft Gardens in Stratford-upon-Avon, England, with the Royal Shakespeare Theatre on the right bank.
Photo©: Anna Fishman / Olegana Travel Boutique
We travel by private coach throughout, which means the days bend around the group rather than around a timetable.
The Cotswolds are the middle of the trip and the part people are slowest to leave. Hidcote, one of the most influential gardens in England. Stratford-upon-Avon and Shakespeare's birthplace. Honey-colored villages, and long evenings on an estate up in the hills.
The last stretch is Highclere Castle for the Downton Abbey morning, then Hampton Court Palace and its gardens, and then Windsor, where the tour ends. The castle, the town, and a final dinner with nobody having to pack for an early start.
A private dining and wine event in a glass-walled venue overlooking a city skyline.
Photo©: Anna Fishman / Olegana Travel Boutique
Every detail is handled: the accommodation, the private guiding, the transport, the dinners, and the access that is not available to somebody arriving with a ticket. For anyone who wants more time, we can build a custom extension in Edinburgh before the tour begins, or in London after it ends.
Book a Complimentary Call with Anna
For women who travel with intention
These small group trips are expertly designed for women who have seen the world yet still seek what feels genuine and new. They’re about rediscovering wonder in food, in place, and in yourself.
Don’t just dream it, experience it!
Anna Fishman, the visionary and soulful force behind Olegana Travel Boutique, orchestrates transformative journeys where meticulously curated adventures meet authentic connection and exquisite, bespoke exploration.
Photo©: Dania Sander / Unique Focus Photography
Join a women’s small group tour with Olegana Travel Boutique: where culture, community, and comfort truly come together.
Grab a time on Anna’s calendar for a free consultation here!
Disclaimer: The information provided in this blog post is for general informational purposes only. All content is provided in good faith; however, we make no representation or warranty of any kind, express or implied, regarding the accuracy, adequacy, validity, reliability, availability, or completeness of any information. The views and opinions expressed in this post are those of the author and do not necessarily reflect the official policy or position of any other agency, organization, employer, or company.
Readers are encouraged to do their own research and consult with a qualified professional before making any decisions based on the content of this blog.